Two Tall Guys Talking Sales

Kevin Lawson and Sean O'Shaughnessey
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"Two Tall Guys Talking Sales," where Sean O'Shaughnessey and Kevin Lawson discuss a single sales topic. Kevin and Sean together have about 60 years of experience in professional selling. This podcast helps people in sales, sales leadership, and business leadership or company owners realize the maximum value of their company by improving their revenue generation capability. This podcast is designed to help those people enhance their companies' sales management practices, methodologies, processes, teams, and messaging. Sean O'Shaughnessey and Kevin Lawson are Fractional Vice Presidents of Sales. They operate their own companies separately but have partnered for this podcast to advise salespeople and SMB companies on successful strategies and methodologies. Kevin is the CEO of Lighthouse Sales Advisors. Lighthouse Sales Advisors is a sales leadership solution provider for small businesses. Lighthouse helps business owners navigate the potential pitfalls around sales growth, sales turnaround, or scaling up by leveraging sales acumen and decades of experience to build effective sales teams. https://www.lighthousesalesadvisors.com/ Sean is the CEO of New Sales Expert. He helps company owners realize the maximum value of their company by improving their revenue generation capability. He helps owners enhance their sales management, methodologies, processes, teams, and messaging.

  1. 2d ago

    Sindre Haaland Coaches on Managing the Game, Not the Scoreboard: Building Predictable Sales Performance

    Sales teams rarely fail because the quota was unclear. They fail because the daily behaviors required to reach it were never defined, measured, or reinforced. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey speak with Sindre Haaland, founder and CEO of SalesScreen, about why effective sales management requires leaders to manage the game, not merely watch the scoreboard. The conversation explores sales gamification, revenue architecture, CRM adoption, qualification discipline, and how AI can support more predictable B2B revenue generation without removing the human motivation that drives consistent execution. Key Topics Discussed Why sales leaders must manage the game, not the scoreboard — 01:19 Revenue targets tell salespeople where they are expected to finish, but they do not explain how to get there. Sindre argues that sales success begins by translating the quota into controllable, revenue-generating activities: calls, meetings, qualified opportunities, pipeline creation, and consistent execution throughout the quarter. Using gamification to change behavior—not merely celebrate outcomes — 02:19 Most sales contests reward closed business, but a salesperson cannot always control when a complex deal closes. Effective gamification focuses instead on meaningful behaviors that sellers can execute every day. Applied correctly, it can improve motivation, consistency, pipeline velocity, and performance among the middle of the sales team, not just recognize the top performers. Connecting activity metrics to conversion quality — 04:07 More activity is not automatically better activity. Measuring calls without examining results can produce meaningless behavior and distorted data. Sean, Kevin, and Sindre discuss the importance of combining activity targets with conversion rates, opportunity progression, and clear definitions of what good execution looks like. Building energy, recognition, and teamwork across the sales organization — 05:25 Sindre describes the moment SalesScreen demonstrated how software could create excitement throughout a sales floor when a deal closed. The larger lesson goes beyond celebration: real-time recognition helps managers reinforce productive behavior, improve engagement, and ensure individual accomplishments are not overlooked inside large sales organizations. Reverse-engineering the quota through revenue architecture — 08:15 Many sales teams know their targets but have never calculated how many calls, meetings, opportunities, and conversions are required to reach them. Without that basic revenue management discipline, prospecting becomes inconsistent, and the pipeline follows a predictable boom-and-bust cycle. Strong sales processes create continuity before pipeline weakness becomes a forecasting crisis. Gamifying qualification and opportunity progression in complex B2B sales — 09:25 In enterprise sales, closed deals may occur too infrequently to serve as useful daily performance signals. Teams can instead quantify progress through qualification frameworks such as MEDDPICC and SPICED, including CRM completeness, opportunity advancement, metric validation, and buying committee coverage. This creates better sales coaching data while reinforcing the behaviors that move complex deals forward. Key Quotes Sindre Haaland — 01:25 "Managers get one thing wrong: they're managing the scoreboard versus managing the game." Sindre Haaland — 04:07 "If you want to change behavior, you need to be in control of those behaviors." Sean O'Shaughnessey — 03:13 "The things you do at the beginning are going to affect the things that you do two, three, four, six, or ten months from now." Sindre Haaland — 08:27 "You need to understand how to get to goal and what real activity you need to put in, day in and day out, to get there." Kevin Lawson — 13:44 "Managing the game, not the scoreboard, is a key behavior." Additional Resources Sindre Haaland CEO and Founder at SalesScreen can be contacted on LinkedIn at linkedin.com/in/shaaland/ SalesScreen A sales performance management and gamification platform designed to quantify sales processes, reinforce productive activity, increase CRM engagement, and create more predictable sales performance. MEDDPICCC A qualification framework commonly used in enterprise sales and complex deals to evaluate metrics, the economic buyer, decision criteria, decision process, paperwork process, goal identification, coaches, champions, and competition. SPICED A sales qualification and discovery framework that helps sellers understand a buyer's situation, pain, impact, critical event, and decision process. A Significant Actionable Item from this Podcast Choose one sales role and reverse-engineer its quarterly quota into a weekly activity model. Start with the revenue target, then calculate the required number of closed deals, qualified opportunities, first meetings, and prospecting activities based on actual conversion rates. Do not stop at activity volume. Add at least one quality measure at each stage, such as meeting-to-opportunity conversion, MEDDPICC completion, stakeholder engagement, or opportunity progression. Once the model is built, ask a harder question: Are managers coaching these controllable behaviors every week, or are they simply reviewing the forecast after the damage has already been done? That distinction determines whether the organization is practicing sales management or merely reporting revenue history. Summary This episode challenges one of the most persistent weaknesses in B2B sales leadership: setting an ambitious target without building the operating system required to achieve it. Sindre Haaland explains how thoughtful gamification, disciplined sales processes, CRM data, and AI-supported performance insights can help leaders reinforce the right behaviors before the quarter slips away. For VPs of Sales, RevOps leaders, AEs, SDR managers, and business owners seeking better pipeline predictability, stronger CRM adoption, and measurable gains in sales productivity, this conversation provides a practical framework for turning quotas into consistent execution. Listen to the episode to learn why predictable revenue does not begin with the forecast; it begins with the behaviors your team repeats every day. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com   You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/   You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/   You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin   You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

  2. Jul 21

    Stop Asking Bad Discovery Questions: How Top B2B Sellers Earn Buyer Trust

    Most sales discovery questions fail before the buyer even answers them. Questions such as "What keeps you up at night?" and "What challenges are you facing?" have been used so often that buyers respond almost automatically, giving sellers little useful insight. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey challenge sales professionals to replace generic scripts with informed, business-specific questions that improve discovery, uncover operational consequences, and help buyers think differently about their problems. They also explain how artificial intelligence and Generative AI can help sellers prepare deeper question paths, navigate Complex Deals, and establish themselves as trusted advisors rather than interchangeable vendors. Key Topics Discussed Why generic discovery questions produce generic answers — 00:00 Kevin and Sean open by dismantling familiar questions such as "What are your goals?" and "What keeps you up at night?" Buyers have heard these questions hundreds of times. Strong discovery must demonstrate Business acumen, industry knowledge, and a genuine understanding of the customer's operating environment. Researching the customer's business before discovery — 01:51 Public information about industries, competitors, economic pressures, and business trends is readily available. Sellers should use frameworks such as PESTEL and the Business Model Canvas to understand what drives the prospect's economics, how the company creates value, and where a proposed solution might improve Revenue generation, ROI, or operational performance. Using operational questions to expose real business problems — 03:11 Kevin illustrates how questions about month-end close procedures, manual spreadsheets, reporting delays, and disconnected Sales processes can produce a meaningful conversation. The goal is not merely to identify which system a prospect uses. It is to uncover the consequences, workarounds, handoffs, and hidden costs that make change valuable. Using AI to create better discovery question paths — 05:58 Sean presents a practical method for using ChatGPT, Claude, Gemini, Copilot, or another AI platform to develop branching discovery questions. Instead of asking an AI tool for one generic question list, sellers can ask it to anticipate several possible buyer answers and then generate the appropriate follow-up questions for each response. This turns AI prompts for B2B sales prospecting into preparation for a real business conversation rather than superficial personalization. Teaching the customer how to buy — 07:00 In Enterprise Sales, buyers often understand their current situation better than they understand the process of selecting and implementing a new solution. Sellers must guide the Buying Committee through workflow changes, implementation tradeoffs, user concerns, and expected outcomes. This is where Value selling becomes practical: the seller connects the solution to the customer's processes, risks, and desired business results. Improving questions through sales management and peer coaching — 10:03 Kevin explains how a VP of Sales or sales manager can improve discovery without simply criticizing the team's existing questions. Questions should be evaluated based on whether they advance the next step, increase deal value, improve Pipeline Velocity, or strengthen the seller's competitive position. Sales Enablement can also become more effective when AEs, SDRs, and sales leaders exchange successful questions and discuss the order in which they should be asked. Key Quotes Kevin Lawson — 00:00 "Buyers have heard these questions hundreds of times, and they answer them on autopilot." Sean O'Shaughnessey — 00:45 "Questions that show that you understand the business… force your customer or your prospect to have a clearer thought process." Sean O'Shaughnessey — 09:00 "You know more about selling your product than they know about buying your product. You have to lead them through the way." Kevin Lawson — 12:03 "Stop asking questions the buyer has already heard. Start asking the questions that get the buyer to say, 'I've never thought about that.'" Additional Resources PESTEL analysis: A framework for examining the political, economic, social, technological, environmental, and legal forces influencing an industry. Business Model Canvas: A tool for understanding how a company creates, delivers, and captures value. The Challenger Sale: A sales methodology centered on teaching customers something valuable, tailoring the conversation, and leading the buying process. Generative AI platforms: ChatGPT, Claude, Gemini, and Microsoft Copilot can help sellers research industries, anticipate buyer responses, and develop stronger discovery questions. B2B Sales Lab: A community where sales professionals and sales leaders can develop their sales acumen, discuss active opportunities, and improve their approach to B2B sales. A Significant Actionable Item from this Podcast Create a branching discovery question bank for one customer segment or active opportunity. Begin with five questions you currently ask during discovery. Eliminate any question the buyer could answer without thinking. Then use an AI tool to generate five plausible responses to each remaining question and develop two or three follow-up questions for every response. Do not treat the resulting output as a script. Review it for business relevance, arrange the questions in a logical sequence, and identify which questions reveal operational impact, financial consequences, organizational resistance, and decision criteria. Then compare the question bank with a successful AE, SDR, sales manager, or industry peer. This is a practical form of AI-powered sales coaching and human-in-the-loop automation. AI expands the seller's preparation, but the seller must still apply judgment, listen carefully, and decide which path to pursue. Done well, the exercise improves Sales success, supports B2B sales pipeline predictability, and helps accelerate Complex Deals without replacing the human conversation. Summary Strong discovery is not a contest to see who can ask the cleverest question. It is evidence that the seller understands the prospect's business well enough to uncover something the buyer has not fully considered. In this episode, Kevin and Sean show how better research, disciplined questioning, sales management coaching, and Generative AI can help sellers move beyond scripted conversations and into meaningful business diagnosis. For sales professionals who want to strengthen their Messaging, improve Value selling, navigate multi-stakeholder deals, and earn the position of trusted advisor, this episode offers a direct and highly practical approach. Listen before your next discovery call—and reconsider every question that allows the buyer to answer on autopilot. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com   You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/   You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/   You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin   You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

  3. Jul 14

    Weak Sales Discovery Creates a Weak Pipeline

    Discovery is not a preliminary conversation before the "real" selling begins. It is where complex B2B deals are either built on credible business value—or quietly undermined by weak assumptions, missing stakeholders, artificial urgency, and an unreliable forecast. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey examine why strong discovery is essential to value selling, accurate revenue management, and sales success. They also explain how experienced sellers use business acumen to uncover operational constraints, quantify ROI, navigate the buying committee, and guide customers through decisions they may not yet understand how to make. Key Topics Discussed Why weak discovery creates a weak pipeline — 00:28 Poor discovery does not merely cause an awkward sales meeting. It produces shallow opportunities, fake urgency, premature proposals, discount pressure, inaccurate forecasts, and stalled decisions. Sean and Kevin establish discovery as the foundation of effective sales processes and B2B sales pipeline predictability. Understanding the business reason behind the purchase — 01:27 Knowing what the buyer wants is not enough. Sellers must uncover why the organization needs it, what business problem is driving the investment, who holds influence and authority, and what happens if the problem remains unresolved. This is where business acumen and value selling begin—and where the seller gathers the evidence needed to defend price and demonstrate ROI later in the deal. Why quoting without discovery makes the salesperson expendable — 02:43 Kevin challenges sellers who rush to educate the prospect, demonstrate features, and produce a quote. If the seller's contribution is limited to product information and pricing, the buyer can often replace that salesperson with a website, product sheet, or artificial intelligence tool. Discovery is what separates professional selling from order processing. Finding the hidden requirements that can derail complex deals — 04:28 A new CNC machine may require more than equipment and installation. Floor space, structural changes, utilities, drainage, environmental requirements, permits, contractors, and operational disruption may all affect the buying decision. In enterprise sales, the apparent purchase is often only one component of a much larger initiative. Effective discovery exposes those dependencies before they destroy pipeline velocity. Using expertise to guide the customer's buying process — 07:53 The seller has typically sold the solution more often than the customer has purchased it. That experience creates an obligation—and an advantage. By identifying questions the buyer has not considered, mapping the buying committee, and navigating multi-stakeholder deals, the salesperson becomes a trusted guide rather than another vendor competing on features and price. How discovery improves forecasting, marketing, and revenue generation — 08:49 Robust discovery strengthens more than the individual opportunity. It improves forecast integrity, exposes the true urgency of the problem, creates better feedback loops with marketing and RevOps, and helps the organization attract more qualified prospects. Weaknesses introduced during discovery inevitably reappear during proposals, negotiations, implementation planning, and closing. Key Quotes "Discovery is not just the stage of the sales process. Discovery is the foundation of the very deal." — Sean O'Shaughnessey, 00:44 "If you're just doing a volume of quoting with no discovery, your job is in jeopardy. Discovery is what separates us from a product sheet." — Kevin Lawson, 03:56 "You have sold your product more than your customer has bought your product. You know more about selling your product than they know about buying your product." — Sean O'Shaughnessey, 08:08 "Anything you do poorly in discovery is going to show up in the proposal, timeline, close, and negotiation stages." — Kevin Lawson, 10:09 Additional Resources Sean also discusses the B2B Sales Lab, a community where salespeople, sales leaders, founders, AEs, SDRs, and VPs of Sales can discuss active selling challenges, improve their sales strategies, and participate in live office-hours conversations with Kevin and Sean. Visit: b2b-sales-lab.com A Significant Actionable Item from this Podcast Before advancing to your next meaningful opportunity, conduct a discovery-gap review. Write down the business problem, the measurable financial or operational impact, the cost of inaction, the decision-making process, the economic buyer, the key influencers, the implementation requirements, and any external dependencies that could delay approval or execution. Do not rely on impressions. Identify what you know, what you have merely assumed, and what remains unanswered. Then use the next customer conversation to close the highest-risk gaps before preparing a detailed proposal or committing the opportunity to the forecast. This single discipline can improve value messaging, reduce unnecessary discounting, expose weak opportunities, and prevent late-stage surprises. Summary Strong discovery gives a seller more than information. It provides the business case, stakeholder map, implementation reality, urgency, and financial logic required to move a complex deal forward. In this episode, Kevin and Sean show why discovery is central to sales management, value selling, forecast accuracy, and sustainable revenue generation—and why skipping it creates problems that no proposal, discount, AI-powered sales coaching platform, or sales enablement strategy can repair later. Listen to the episode before your next discovery meeting, and reconsider whether you are genuinely helping the customer make a sound decision or simply gathering enough information to produce a quote. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com   You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/   You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/   You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin   You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

  4. Jul 7

    Happy 250th Birthday, America

    No big topics in this episode. Just a quick acknowledgment that the United States of America is now 250 years old.  Go back to your family and enjoy your time with them. Check us out next week when we will be sharing great sales advice again.

  5. Jun 30

    Should Sales Leaders Reset Quotas at Midyear

    Midyear exposes the truth in every sales organization. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey tackle a problem many business owners, sales leaders, and salespeople quietly face at the halfway point of the year: unclear goals, weak commission plans, soft pipeline discipline, and the temptation to reset expectations instead of fixing the sales processes that created the gap. This is a practical conversation about B2B sales management, quota accountability, revenue generation, pipeline prioritization, and the uncomfortable but necessary work required to improve sales success in the second half of the year. Key Topics Discussed Midyear goal setting when the original plan was missing or unclear — 00:00 Sean explains why some companies reach July without properly documented sales goals or commission plans. The corrective action is not complicated, but it is often avoided: write the plan down, align compensation with company priorities, and make sure salespeople know exactly how they are being measured. Why sales leaders should not casually reset the goal — 02:14 Kevin argues that adjusting the target downward can create a dangerous management precedent. If the number was the right number, the job is to solve the gap through better sales strategies, qualification, activity, referrals, and pipeline focus—not move the scoreboard. The rare exception to keeping the original quota — 06:34 Sean adds an important leadership caveat. If the CEO or executive team built the number around a product launch, acquisition, market event, or business assumption that never materialized, that is not a salesperson's problem. That is an executive planning problem, and it should be handled honestly. Pipeline rationalization and better qualification — 09:57 Kevin walks through the discipline of deciding which deals deserve time and which ones do not. Complex deals, unclear next steps, bad-fit opportunities, and stalled prospects all consume selling capacity. Better qualification improves pipeline velocity by giving salespeople time back to pursue better opportunities. Time management, delegation, and protecting prospecting time — 13:43 Sean warns against the classic sales rollercoaster: closing current business while starving future pipeline. Whether a company uses SDRs, AEs, business development resources, or full-cycle salespeople, every stage of the sales process needs dedicated time. Revenue management requires knowing where the week actually went. Key Quotes Sean O'Shaughnessey — 01:14 "You didn't get it done at the first of the year. That doesn't mean you can't do it now." Kevin Lawson — 03:40 "You never adjust the goal. Your job as a salesperson is to hit the goal or your quota." Sean O'Shaughnessey — 08:34 "Salespeople can't make their goals for things that are outside of their control." Kevin Lawson — 10:22 "You've got to figure out which deals are aligned and which ones are not aligned to what you do." Sean O'Shaughnessey — 14:03 "We were so busy selling that we forgot to sell." Additional Resources EOS implementers — referenced as part of the broader business coaching and planning conversations happening at midyear. FocalPoint and ActionCOACH — mentioned as examples of coaching organizations business owners may turn to when trying to catch up or plan ahead. Microsoft PTAP — referenced by Kevin as "plan to exceed plan," a useful framing for quota planning and sales performance management. MEDDPICCC, BANT, and SPICED-style qualification methodologies — referenced as examples of structured approaches to qualification, deal inspection, and sales process discipline. Marketing-generated digital assets — discussed as one practical source of conversation creation when salespeople are behind and need to rebuild pipeline coverage. A Significant Actionable Item from this Podcast Audit your pipeline and calendar before changing the goal. Identify every active opportunity, mark which deals have clear next steps, remove or deprioritize poor-fit opportunities, and block time this week for prospecting, referral requests, outreach to past customers, and networking. Do not rely on optimism. If an opportunity does not match your ideal customer profile, lacks buyer commitment, or requires too much customization to win, it is likely stealing time from better revenue-generating work. Summary This episode is a timely midyear inspection for any B2B salesperson, VP of Sales, business owner, or sales management leader who is trying to protect the second half of the year. Kevin and Sean make a clear argument: missed goals are not solved by pretending the number changed. They are solved by stronger qualifications, clearer commission plans, better time allocation, disciplined sales processes, and more honest pipeline review. If you are behind, ahead, or unsure where you really stand, this conversation will help you decide whether you have a quota problem, a planning problem, a pipeline problem, or a leadership problem—and what to do next.

  6. Jun 23

    From Marine Recon to Venture Capital: Paul Claxton on Sales Strategy, AI, and Founder Readiness

    In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey sit down with Paul Anthony Claxton of Digirati Investments for a sharp conversation on venture capital, founder readiness, sales architecture, and why early-stage companies cannot hide behind product obsession or incomplete data. Paul brings a rare blend of Marine Corps reconnaissance discipline, sales leadership, investment judgment, and AI perspective to the table. The result is a fast-moving discussion about Business acumen, customer conversations, market intelligence, Sales processes, and the practical realities of Revenue generation when founders are trying to build something the market may not yet know it needs. Key Topics Discussed Founder adaptability and the path from Marine to venture capitalist — 00:20 Paul explains how adaptability, opportunity recognition, and power networking shaped his move from the Marines into venture capital. His point lands hard for anyone in sales management: the best salespeople and founders do not simply follow the plan. They adjust when the market, the customer, or life changes direction. Why investors look beyond the product — 02:19 Paul discusses what he looks for when evaluating founders and companies. Product matters, but it is not enough. Founders need to understand macroeconomics, microeconomics, contracts, deal structure, customer impact, and the broader commercial environment. That is where Business acumen becomes a serious differentiator. Inventing necessity and creating surrounding market demand — 03:24 Paul introduces Digirati Investments' phrase "inventing necessity" and explains why strong products do more than solve one isolated problem. They create adjacent needs, new sub-industries, and additional opportunities for Revenue generation. This is a useful framing for founders, sales leaders, and anyone building Sales strategies around emerging markets. The danger of product-centric founders — 04:43 Sean pushes into a critical founder question: how often do companies believe they have a market-changing product before they have validated the market? Paul's answer is direct. Too many founders are product-centric instead of people-centric. Real Sales success starts with human conversations long before the product is fully built. Data, AI, and consultative selling in modern sales ecosystems — 05:33 Paul argues that strong data flow is essential, but data alone cannot replace human interaction. He connects AI, CRM automation, customer engagement, and consultative selling to a broader point: modern Sales processes need both high-quality data and high-quality conversations. Reconnaissance, competitor intelligence, and explainable AI — 09:15 Drawing from his Marine background, Paul explains why companies must gather intelligence from both customers and competitors. AI can support that work, but leaders must understand where the data came from and whether it reflects the actual market. Bad assumptions create bad Messaging, weak qualification, and flawed Revenue management decisions. Key Quotes Paul Anthony Claxton — 00:35 "The best salespeople are the most adaptable people." Paul Anthony Claxton — 05:33 "A lot of times I'll run across founders that are product-centric instead of being people-centric." Sean O'Shaughnessey — 08:41 "How do you know that what you're doing is going to work if you don't have salespeople out pre-talking and pre-building up what that problem is?" Paul Anthony Claxton — 09:15 "If you don't have people gathering reconnaissance, it's not just talking to who you think your prospective customers are, but it's also understanding how your competitors qualify." Kevin Lawson — 11:49 "Not only do we have to know as sellers who our total addressable market is, but our service obtainable market is, but it's important to keep that data current." Additional Resources Paul Anthony Claxton — Venture capitalist, U.S. Marine, sales architecture thinker, and guest on this episode. https://www.linkedin.com/in/businessmanathletemarine/ Digirati Investments — Paul's investment firm, discussed in the episode through the lens of "inventing necessity." Explainable AI — Paul's podcast, referenced during the conversation about understanding the origin, quality, and accuracy of AI-driven data. PaulClaxton.io — Paul's personal website, where you can learn more about his work, investments, and related ventures. A Significant Actionable Item from this Podcast Before investing more time, money, or sales effort into a product, schedule direct market conversations with prospective customers and competitive intelligence reviews. Do not rely only on internal conviction, CRM data, AI summaries, or founder enthusiasm. Validate the problem, study how competitors qualify and sell, and pressure-test whether your Value selling story connects to a real business need. This one discipline improves Sales strategies, sharpens Messaging, and prevents companies from building sales motions around assumptions the market has not confirmed. Summary This episode is a compact but high-value conversation for founders, investors, sales leaders, and anyone responsible for Revenue generation in an uncertain market. Paul Anthony Claxton brings a different lens to sales and investment evaluation: part Marine reconnaissance, part venture capitalist, part sales architect. Kevin and Sean guide the discussion into the practical questions that matter most: Does the founder understand the market? Is the product creating real necessity? Is the data explainable? Are customer conversations happening early enough to shape the business before money and time are wasted? Listen to this episode of Two Tall Guys Talking Sales if you want a sharper view of founder readiness, modern sales management, AI-informed selling, and the kind of Business acumen required for durable Sales success.   B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com   You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/   You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/   You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin   You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

  7. Jun 16

    Stop Wasting Time on Bad Deals: Sales Management Lessons for a Cleaner Pipeline

    In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey take on one of the most expensive problems in B2B selling: pipeline clutter. Sellers have limited customer-facing time, and too much of it gets wasted chasing deals that were never truly qualified, never aligned with the ideal client profile, or never likely to close. Kevin and Sean dig into the math, mindset, and sales management discipline required to protect selling time, improve forecast accuracy, and focus on the right opportunities. This conversation connects time management, Business acumen, Sales strategies, Sales processes, Value selling, Messaging, Revenue management, and Revenue generation into one practical question: Are you spending your limited sales time on deals that can actually produce Sales success? Key Topics Discussed Why seller time is the most valuable sales resource — 00:00 Kevin opens the episode by pointing out that only a fraction of a seller's week is spent directly with customers. The rest disappears into research, reporting, scoping, internal meetings, travel, and administrative drag. That makes time management a revenue issue, not a productivity slogan. How to identify deals that do not belong in your pipeline — 01:14 Sean challenges sellers to open their CRM and look honestly at the deals expected to close in the next quarter or six months. Do they fit the ideal client profile? Do they look like the kinds of customers the company wins? Or are they sitting in the pipeline because the seller hopes they might become something? Using quota math to evaluate opportunity cost — 02:45 Sean breaks the problem down to simple math: take the seller's annual working hours, divide by the quota, then adjust for actual customer-facing time. The farther a prospect is from the ideal client profile, the more time it typically consumes. That raises the real question: could the seller create more revenue by focusing on easier, better-fit deals? The danger of an aspirational pipeline — 04:12 Kevin explains how inflated pipelines create false confidence, poor forecasting, and bad leadership conversations. A pipeline full of hope does not create commissions. A pipeline full of qualified, workable, attainable deals gives sales leaders and sellers better data for decision-making. Discovery discipline and hard qualification questions — 07:07 Kevin emphasizes the importance of asking hard questions early. Budget, business pain, decision authority, and the pain of change must be tested before a deal moves too far forward. If a seller has issued a proposal to someone who cannot buy, does not control the budget, or cannot define the business problem, the sales process has already drifted. Becoming your own sales manager — 08:48 Sean pushes sellers to manage their own pipeline with the same honesty they would expect from a strong sales leader. The best salespeople ask themselves whether a deal is real, whether it is efficient, whether it has access, whether the buyer is engaged, and whether it belongs in this year's forecast at all. Key Quotes Kevin Lawson — 00:00 "As sellers, people who are chasing a quota every year, we have one thing that is so precious that it is absolutely paramount for us to pay attention to, and that's our time." Sean O'Shaughnessey — 01:14 "We all know that if we had more time to call on great customers, we'd probably make more money. So let's talk about calling on great customers." Kevin Lawson — 05:46 "Your commission is driven by your accuracy of closes, not your aspirations. Aspirational deals don't turn into commissions." Sean O'Shaughnessey — 09:09 "The best salespeople are great independent sales managers of themselves." Kevin Lawson — 12:09 "Simply quota, close rate, number of deals, average deal size. That's really all you need, and it's all stuff that's in your pipeline now." Additional Resources B2B Sales Lab — Sean mentions that sellers can use the B2B Sales Lab to pressure-test pipeline questions, get peer feedback, and discuss whether specific opportunities deserve more time and attention. Join the Lab at b2b-sales-lab.com CRM pipeline review — The episode repeatedly encourages sellers to use their CRM as the source of truth for examining deal fit, timing, stage accuracy, close probability, and forecast quality. Ideal Client Profile — Kevin and Sean reinforce the importance of understanding which prospects fit the company's best customer profile and which ones sit too far outside the target to justify the time required. Customer Interaction Hours episode — Kevin refers listeners back to a previous discussion in which Sean explained customer interaction hours and why increasing time in front of the right buyers improves the win position. Quarterly Business Reviews — Kevin notes that past customers and QBRs can help sellers and sales leaders identify strategic conversations, referral opportunities, and ways to generate more of the right pipeline. A Significant Actionable Item from this Podcast Before your next pipeline review, identify three deals in your CRM that do not clearly fit your ideal client profile, lack decision-maker access, have weak urgency, or keep slipping from one forecast period to the next. For each one, decide whether it should stay active, move to a future follow-up task, or be disqualified. Then have the direct conversation with the buyer: "It does not seem like this is a priority right now. Should we pause this and revisit it later?" That single question protects your time, improves forecast accuracy, and forces cleaner revenue management. Summary This episode is a practical reminder that sales success is not created by carrying a bigger pipeline; it is created by carrying a more honest one. Kevin and Sean show why bloated pipelines waste time, damage forecasts, and distract sellers from the deals most likely to generate revenue. The conversation is especially useful for salespeople, sales managers, and company leaders who want better sales processes, sharper qualification, stronger messaging, and more disciplined value selling. If your pipeline looks impressive but does not reliably convert, this episode will challenge you to stop admiring the number and start managing the reality. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com   You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/   You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/   You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin   You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

  8. Jun 9

    Are Your Salespeople in the Wrong Roles? How to Match Talent to Revenue Growth

    Two Tall Guys Talking Sales takes a practical look at one of the most common sales management mistakes: assuming all salespeople are built for the same job. Sean O'Shaughnessey and Kevin Lawson use a basketball analogy to unpack the difference between hunters, farmers, lone wolves, challengers, relationship sellers, transactional sellers, and trappers. This episode challenges owners, sales leaders, and frontline sellers to examine whether their sales processes, compensation plans, and revenue management expectations actually match the type of salesperson required for Sales success. If your team is underperforming, the issue may not be a lack of effort. It may be role design. Key Topics Discussed 01:00 — Why Sales Roles Need Clear Definitions Sean opens with a basketball analogy: if you do not understand the positions, the game becomes harder to follow. The same is true in sales. Confusing labels like hunter, farmer, challenger, lone wolf, and trapper can create bad hiring decisions, poor coaching, and broken sales strategies. 02:50 — Do Not Confuse Seller Type with Business Model Kevin draws an important distinction between the kind of salesperson you have and the kind of business you operate. A transactional sales model, a relationship-driven sales model, and an enterprise sales model each require different selling behaviors, messaging, and support structures. 06:20 — Hunters, Farmers, and the Cost of Misalignment Sean explains why a one-time ERP-style sale usually requires a hunter, while repeat-purchase relationships often require a farmer. Asking one type of salesperson to behave like another may be possible, but it is rarely efficient. Sales leaders need Business acumen to know what role the business actually requires. 08:25 — Lone Wolves, Challengers, and Unsupported Sales Teams The discussion turns to lone wolves and challengers, especially in organizations that give salespeople little infrastructure, weak marketing, poor sales processes, or minimal sales enablement. If leadership expects sellers to "just figure it out," they may be selecting for independence while unintentionally creating risk. 09:50 — How to Reshape a Sales Team Without Blowing It Up Kevin warns against the instinct to immediately replace the team. The better move is to take an intellectually honest look at the team's structure, upskill where possible, and decide whether the business needs account managers, customer service support, hunters, or relationship-focused sellers. 12:50 — The Trapper: Building Toward Enterprise Revenue Generation Sean closes by describing the trapper: the salesperson who can hunt, farm, lead, challenge, and plan proactively for larger future opportunities. This is where Value selling becomes more than a technique. It becomes a disciplined approach to expanding from a pilot project to departmental adoption, divisional traction, and eventually enterprise-level revenue generation. Key Quotes Sean O'Shaughnessey — 01:07 "Not knowing what the roles are is a big deal. So that same kind of thing happens in a sales arena, where you may not understand what type of salesperson you have or what type of salesperson you need." Kevin Lawson — 02:51 "It's important to note that just because somebody looks like something doesn't mean that's actually what they are." Kevin Lawson — 03:51 "You, as a seller, need to understand your business model so that you know how to sell." Sean O'Shaughnessey — 08:08 "Asking one type of salesperson to be another is really difficult to do. That's like asking that point guard to be the center." Kevin Lawson — 10:39 "Change people before you have to change people." Sean O'Shaughnessey — 14:15 "How do you become proactive? How do you plan for the deal that's going to happen in nine months?" Additional Resources The Challenger Sale — Referenced during the discussion of lone wolves and challengers, especially the idea that some sellers succeed by taking control of complex customer conversations. Eliminate Your Competition by Sean O'Shaughnessey — Sean refers to the "trapper" concept from his book as the more complete sales archetype for complex, enterprise-level selling. B2B Sales Lab — Kevin mentions that this topic will be explored further in B2B Sales Lab office hours, where sellers and sales leaders can dig into the practical work of assessing team fit, role design, and sales execution. A Significant Actionable Item from this Podcast Audit your current sales team against the sales motion your business actually requires. Do not start with personality labels. Start with the business model. Are you selling once and moving on? Are you expanding accounts over years? Are your deals transactional, relationship-driven, enterprise-level, or a mix? Then map each salesperson against the role the business needs: hunter, farmer, account manager, challenger, lone wolf, or trapper. The decision that follows is the real work. Some people need coaching. Some need a different seat. Some roles need compensation redesign. Some teams need additional support around account management, customer success, prospecting, or CRM discipline. Sales success improves when the revenue management system fits the people, the process, and the customer buying motion. Summary This episode of Two Tall Guys Talking Sales is a useful listen for any owner, VP of Sales, sales manager, or seller who has ever wondered why a capable salesperson still struggles in the wrong role. Kevin Lawson and Sean O'Shaughnessey make the case that sales performance is not only about talent. It is about fit, structure, expectations, and leadership discipline. If your sales strategies are not producing the results you expected, this conversation will help you look beyond activity levels and ask the more important question: Do we have the right people in the right sales roles for how our customers actually buy? B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com   You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/   You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/   You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin   You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/

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Ratings & Reviews

5
out of 5
7 Ratings

About

"Two Tall Guys Talking Sales," where Sean O'Shaughnessey and Kevin Lawson discuss a single sales topic. Kevin and Sean together have about 60 years of experience in professional selling. This podcast helps people in sales, sales leadership, and business leadership or company owners realize the maximum value of their company by improving their revenue generation capability. This podcast is designed to help those people enhance their companies' sales management practices, methodologies, processes, teams, and messaging. Sean O'Shaughnessey and Kevin Lawson are Fractional Vice Presidents of Sales. They operate their own companies separately but have partnered for this podcast to advise salespeople and SMB companies on successful strategies and methodologies. Kevin is the CEO of Lighthouse Sales Advisors. Lighthouse Sales Advisors is a sales leadership solution provider for small businesses. Lighthouse helps business owners navigate the potential pitfalls around sales growth, sales turnaround, or scaling up by leveraging sales acumen and decades of experience to build effective sales teams. https://www.lighthousesalesadvisors.com/ Sean is the CEO of New Sales Expert. He helps company owners realize the maximum value of their company by improving their revenue generation capability. He helps owners enhance their sales management, methodologies, processes, teams, and messaging.

Information

  • Creator
    Kevin Lawson and Sean O'Shaughnessey
  • Years Active
    2023 - 2026
  • Episodes
    198
  • Rating
    Clean
  • Copyright
    © 2024
  • Show Website
    Two Tall Guys Talking Sales